An AI that asks questions?
You are referring to 'proactive AI' as opposed to 'reactive AI' like Alexa, Cortana, Siri, Bixby, Google Assistant, and others.  There hasn't been much progress in this area of AI.  Google's recent demonstration of Duplex addresses this to some extent.  Some chatbots are proactive. Genesys provides such capability.  Check out their video

Azure's bot service has a page on how to implement proactivity and there is another video that walks through the whole process: Learn to build Proactive Bot in 30 Minutes.